October always creates a kind of sartorial dissonance in me. September is never as autumnal as I expect; it’s typically pervaded by late summer weather, and fall doesn’t even technically begin until the last week or so. For about seven days, I whip out my chunkiest knits and coziest scarves, and I trade my saturated summer palette for a more muted, neutral-filled autumn one.

But then October comes. And October demands something darker, spookier and edgier than the rest of autumn. The olive greens, camel browns and mustard yellows I pulled out the week before no longer feel appropriate for the season—only the charcoals and blacks do.

I crave the return to fall fashion, but I also want to celebrate October’s haunted-glam aesthetic while I have it. What’s a girl to do—besides assemble an array of monochromatic, black-on-black ensembles, of course?

The shift from “fall’s finally here!” to “all black everything” isn’t an easy one to make. Like I said before, it inspires a kind of dissonance in my autumn-loving-but-also-Halloween-obsessed heart.

‘Tis the season for putting one aesthetic on hold for 31 days while you wholeheartedly embrace another, and I’ve found the best medicine for this struggle typically involves some combination of perusing incredible black-on-black street style looks and shopping the best black pieces retailers have on offer this season.

I’ve already done the latter. (You can find my magnum opus—a shopping guide of 101 next-level black pieces to shop this fall—on our site.) Which means it’s time to do the former. I’m not lying when I say I spent a full Saturday afternoon combing through photos of street style stars wearing nothing but black (all the while casually watching Daria, a cartoon that felt aesthetically and emotionally appropriate for this journey of mine).

I don’t expect anyone else to be so thoroughly affected by this annual style whiplash that they’d actually be willing to part with a precious Saturday afternoon just to look at street style photos (and watch Daria!). So I went ahead and kept track of the highlights—the darkest, witchiest, edgiest looks I came across. And I’ve chronicled them for you below.

If anything, these looks are sure to get you in the October style spirit—and they might just inspire an ensemble or two, too.

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An incredible silhouette made all the more dramatic thanks to some carefully selected black and gold accessories.

Photo: Claudio Lavenia/Getty Images.

The easiest way to dress up athleisure? Layer on a seriously dark cat-eye.